Water → HCID 67552304, compound

HRID 1422133Notes

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-benzisoxazol3-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-b1cf1e399a7f4310b1bbd28d9f270991
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080773

Reaction notes

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