Water → HCID 67552304, compound

HRID 428029Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[C@H:10]([CH:31]([CH3:33])[CH3:32])[NH:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[O:24][N:23]=1)[CH2:13][CH:14]=[CH2:15].O.S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1>[O:24]1[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH:12]([NH:11][CH:10]([CH:31]([CH3:33])[CH3:32])[CH2:9][OH:8])[CH2:13][CH:14]=[CH2:15])=[N:23]1

Participants

Conditions

Temperature: -10 °C

Procedure

Under an atmosphere of nitrogen, 5.6 g of lithium aluminum hydride were added to 500 ml of dry tetrahydrofuran. The mixture was cooled to −10° C. and a solution of 30 g of (S)-N-[1-[2-(1,2-benzisoxazol-3-yl)phenyl]-3-butenyl]-L-valine methyl ester in 500 ml of dry tetrahydrofuran was added slowly. The mixture was stirred at −10° C. for 16 h, after which 22 ml of water was slowly added. After stirring at room temperature for 0.5 h, magnesium sulphate was added. The solids were filtered off and the filtrate was evaporated to dryness under reduced pressure to yield 25 g of [S-(R*,R*)]-2-[[1-[2-(1,2-benzisoxazol-3-yl)phenyl]-3-butenyl]amino]-3-methyl-1-butanol.

Workup

stirringAfter stirring at room temperature for 0.5 h
filtrationThe solids were filtered off
customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-859f2e5a91f944d38da6d27130d6f7f7
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313139B1

Reaction notes

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