Water → (2R,3R)-3-(benzyloxy)-2-(tritylamino)butan-1-ol

HRID 1035542Notes

Reaction equation

[CH2:1]([O:8][C@H:9]([CH3:35])[C@@H:10]([C:31](OC)=[O:32])[NH:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[CH2:1]([O:8][C@H:9]([CH3:35])[C@H:10]([NH:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:31][OH:32])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl O-benzyl-N-trityl-L-threoninate (4.61 g, 9.91 mmol) was dissolved in 100 mL of anhydrous Et2O and the solution was cooled to 0° C. under N2. Lithium aluminum hydride (2.28 g, 60 mmol) was added and the mixture was stirred for 2 hours. The reaction mixture was then sequentially treated with 2.28 mL of H2O, 2.28 mL of 15% NaOH solution and 6.84 mL of H2O. After stirring for 30 minutes, the reaction mixture was filtered to remove the white solid. The solid was washed with several portions of Et2O and the combined filtrates were concentrated under reduced pressure. Chromatography (SiO2, 10-20% ethyl acetate/hexanes) gave 4.34 g of (2R,3R)-3-(benzyloxy)-2-(tritylamino)butan-1-ol as a colorless syrup.

Workup

stirringAfter stirring for 30 minutes
filtrationthe reaction mixture was filtered
customto remove the white solid
washThe solid was washed with several portions of Et2O
concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record: ord-88ecb6470b1e4cb98fdde34f56637cb0
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546383B2

Reaction notes

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