1-Bromopentadecane → (2S,3S)-2-(N-Benzyloxycarbonylamino)-3-octadecanol

HRID 722822Notes

Reaction equation

HRID 722822 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:15])[CH:13]=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C@@H:13]([OH:14])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])[CH3:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 123941-BromopentadecaneHCID 11790409(S)-(1-Methyl-2-oxo-ethyl)-carbamic acid benzyl ester

Product 1

HCID 58743388(2S,3S)-2-(N-Benzyloxycarbonylamino)-3-octadecanol

Procedure

According to the method of Example 26, from aldehyde 28 (640 mg, 3.1 mmol) and 1-bromopentadecane (5.0 g, 17.2 mmol), alcohol 90 was obtained as a colorless oil (690 mg, 53% yield).

Sources & evidence

ORD record
ord-b8f53c1f74e2406c8f1b6932c228e157
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Reaction notes

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