1-Bromotridecane → (2S,3R)-2-(N,N-Dibenzylamino)-3-hexadecanol

HRID 722804Notes

Reaction equation

HRID 722804 reaction equation
[CH2:1]([N:8]([C@@H:16]([CH3:19])[CH:17]=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>>[CH2:9]([N:8]([C@H:16]([C@H:17]([OH:18])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21])[CH3:19])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 130001-BromotridecaneHCID 11107860(S)-2-Dibenzylamino-propionaldehyde

Product 1

HCID 58743369(2S,3R)-2-(N,N-Dibenzylamino)-3-hexadecanol

Procedure

According to the method of Example 26, from aldehyde 4 (332 mg, 1.31 mmol) and 1-bromotridecane (863 mg, 3.28 mmol), alcohol 33 was obtained as a colorless oil (172 mg, 30% yield).

Sources & evidence

ORD record
ord-e48867949d73470fb71ea1b25ec5fd34
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Reaction notes

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