(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamine → (4S)-1-benzyloxycarbonyl-4-hydroxy-1,2,3,4-tetrahydroquinoline

HRID 407118Notes

Reaction equation

HRID 407118 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(N[C@H]([C@@H](N)C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)=CC=1>>[CH2:1]([O:8][C:9]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@@H:14]([OH:21])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6612782(1S,2S)-(+)-N-p-Tosyl-1,2-diphenylethylenediamineHCID 23726243Benzyl 4-oxo-3,4-dihydroquinoline-1(2H)-carboxylate

Product 1

HCID 16117781(4S)-1-benzyloxycarbonyl-4-hydroxy-1,2,3,4-tetrahydroquinolineYield 86.2%

Procedure

1-benzyloxycarbonyl-4-oxo-1,2,3,4-tetrahydroquinoline (281 mg), [RuCl2(benzene)]2 (25.0 mg) and (S,S)-TsDPEN (73.3 mg) were treated in the same manner as Example 4 to give 244 mg of (4S)-1-benzyloxycarbonyl-4-hydroxy-1,2,3,4-tetrahydroquinoline (optical purity: 97% ee, yield: 86%).

Sources & evidence

ORD record
ord-28a5d71be947481e8d4b5970855d7011
Source dataset
uspto-grants-2014_06
Patent number
US08754221B2

Reaction notes

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