(+/-)-3-(Benzyloxy)-1-(2-chlorophenyl)propane-1,2-diol → (4S,5R)-4-(benzyloxymethyl)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolane

HRID 1506990Notes

Reaction equation

HRID 1506990 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([OH:20])[C@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[Cl:19])[OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21](OCC(O)C(C1C=CC=CC=1Cl)O)[C:22]1C=CC=C[CH:23]=1>>[CH2:1]([O:8][CH2:9][C@H:10]1[C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[O:12][C:22]([CH3:23])([CH3:21])[O:20]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 90026408(+/-)-3-(Benzyloxy)-1-(2-chlorophenyl)propane-1,2-diolHCID 118379121(1S,2R)-3-(benzyloxy)-1-(2-chlorophenyl)propane-1,2-diol

Product 1

HCID 118379134(4S,5R)-4-(benzyloxymethyl)-5-(2-chlorophenyl)-2,2-dimethyl-1,3-dioxolaneYield 85%

Procedure

The substantially same method as described in Example 371 was conducted, except that (1S,2R)-3-(benzyloxy)-1-(2-chlorophenyl)propane-1,2-diol (Preparation example 375) was used instead of that (±)-3-(benzyloxy)-1-(2-chlorophenyl)propane-1,2-diol (Preparation example 370), to obtain the title compound (0.84 g, 85%).

Sources & evidence

ORD record
ord-48f6a140372f46cfa46ad30b0e09c159
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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