Benzylamine → (3S,4R,6S)-6-benzhydryl-4-benzylamino-tetrahydropyran-3-ol

HRID 78936Notes

Reaction equation

HRID 78936 reaction equation
[CH:1]([C@@H:14]1[CH2:20][C@H:19]2[C@H:17]([O:18]2)[CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH:1]([C@H:14]1[O:15][CH2:16][C@@H:17]([OH:18])[C@H:19]([NH:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20]1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 86605349HCID 86605349, compound

Product 1

HCID 11257315(3S,4R,6S)-6-benzhydryl-4-benzylamino-tetrahydropyran-3-olYield 86%

Procedure

(1R,4S,6S)-4-benzhydryl-3,7-dioxa-bicyclo[4.1.0]heptane 28b (0.03 g, 0.09 mmol) reacted with benzylamine (0.20 g, 1.88 mmol) (Procedure E) to yield (3S,4R,6S)-6-benzhydryl-4-benzylamino-tetrahydropyran-3-ol, (−)-29h, 0.03 g (Yield; 86%), [α]D=(−)70.6, c=1, MeOH).

Sources & evidence

ORD record
ord-088e71edff4741ad92f47adb97670064
Source dataset
uspto-grants-2014_09
Patent number
US08841464B2

Reaction notes

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