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

HRID 327340Notes

Reaction equation

HRID 327340 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@H:17]([OH:37])[C@@H:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:22]=2)[NH:19][CH3:20])[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.[CH3:38][O:39][CH:40]([O:43][CH3:44])[CH2:41]Br.C(=O)([O-])O.[Na+]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@H:17]([OH:37])[C@@H:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH2:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:22]=2)[N:19]([CH2:41][CH:40]([O:43][CH3:44])[O:39][CH3:38])[CH3:20])[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

Participants

4

Reactant 3

HCID 816722-Bromo-1,1-dimethoxyethaneHCID 516892Sodium BicarbonateHCID 22849456rel-(1S,2R)-1,2-bis(3'-benzyloxy-4'-methoxyphenyl)-2-methylaminoethanol

Product 1

HCID 11813953rel-(1S,2R)-1,2-bis(3'-Benzyloxy-4'-methoxyphenyl)-2-[(2",2"-dimethoxyethyl)-methyl-amino]ethanol

Procedure

Mixture: 1.40 g 2.8 mmol) of rel-(1S,2R)-1,2-bis(3'-benzyloxy-4'-methoxyphenyl)-2-methylaminoethanol, 0.43 ml (0.61 g, 3.6 mmol) of bromoacetaldehyde dimethyl acetal, 0.71 g (8.4 mmol) of sodium hydrogen carbonate.

Sources & evidence

ORD record
ord-e484ae2d2c62411594c1dae5bb0026aa
Source dataset
uspto-grants-1993_12
Patent number
US05272270

Reaction notes

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