Dichloromethane → (1S,2R)-1,2-bis(3'-Benzyloxy-4'-methoxyphenyl)-2-[(2",2"-dimethoxyethyl)amino]-ethanol

HRID 327336Notes

Reaction equation

HRID 327336 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@@H:17]2[O:35][C@H:18]2[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:20]=2)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][O:37][CH:38]([O:41][CH3:42])[CH2:39][NH2:40].ClCCl>C(O)C>[CH2:28]([O:27][C:21]1[CH:20]=[C:19]([C@H:18]([OH:35])[C@@H:17]([C:11]2[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)[NH:40][CH2:39][CH:38]([O:41][CH3:42])[O:37][CH3:36])[CH:24]=[CH:23][C:22]=1[O:25][CH3:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 89728Aminoacetaldehyde dimethyl acetalHCID 22849458rel-(S,S)-3,3'-dibenzyloxy-4,4'-dimethoxystilbene oxide

Product 1

HCID 22849452(1S,2R)-1,2-bis(3'-Benzyloxy-4'-methoxyphenyl)-2-[(2",2"-dimethoxyethyl)amino]-ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Mixture: 187.2 g (0.4 mol) of rel-(S,S)-3,3'-dibenzyloxy-4,4'-dimethoxystilbene oxide, 210 g (2 mol) of aminoacetaldehyde dimethyl acetal, 5 l of dichloromethane, 3 l of ethanol.

Sources & evidence

ORD record
ord-f096a3d7ac5144d796ec4aed78cb080c
Source dataset
uspto-grants-1993_12
Patent number
US05272270

Reaction notes

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