Lehman Brothers Holdings Inc is seeking Bankruptcy Court permission to make another $255 million debt investment in a New York office building, saying doing so would protect its existing investment.

Lehman already has a $437 million stake in the building, which is located on a valuable stretch of Park Avenue in Midtown Manhattan, according to court documents released on Monday.

The investment bank, which collapsed in September 2008, has filed a motion in New York bankruptcy court to purchase the B note of a senior debt facility, using estate funds.

Lehman had originated some $1.23 billion in loans to finance the purchase of the 21-story building in May 2007. In August, Lehman suspected that Broadway Partners -- the building's owner -- was going to default on the B note and began discussions on a potential restructuring, according to court papers.

Making a new investment in 237 Park by purchasing the B note from the seller has significant upside for Lehman Brothers Holdings and represents the best means of protecting LBHI's current investment, ... which could potentially be wiped out if a party other than LBHI acquires the B note and pursues a foreclosure of the B note, the company wrote in its motion.

U.S. Bankruptcy Judge James Peck on Tuesday ordered a hearing on June 16 to consider the motion.

LBHI in consultation with the official committee of unsecured creditors will seek to purchase the B Note at the most favorable terms possible, said Lehman. However, acquisition of the B Note even at its par value represents a valuable investment for LBHI and its estate.

In addition, Lehman said, buying the note would allow it to protect its other positions in the debt structure and maximize value for its estate.

The documents did not give more details about the possible value and a company spokeswoman declined to give specifics.

We are recommending this investment because we believe it meets the three key criteria we must consider: it has the potential to yield an above-market return, it poses minimal risk exposure and it increases the estate's recovery prospects, Lehman Brothers Holdings' chief executive, Bryan Marsal, said in an e-mailed statement.

Before filing for bankruptcy in September 2008, Lehman was the fourth-largest U.S. investment bank.

The case is in re: Lehman Brothers Holdings Inc et al, U.S. Bankruptcy Court, Southern District of New York, No. 08-13555.

(Editing by Leslie Adler)