(3R,5S)-2-methyl-1-phenylpropan-2-yl 6-chloro-3,5-dihydroxy-hexanoate → 2-methyl-1-phenylpropan-2-yl 2-((4R,6S)-6-(bromomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

HRID 39401Notes

Reaction equation

HRID 39401 reaction equation
[Br:1][CH2:2][C@@H:3]([OH:21])[CH2:4][C@@H:5]([OH:20])[CH2:6][C:7]([O:9][C:10]([CH3:19])([CH3:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8].Cl[CH2:23][C@@H:24](O)[CH2:25][C@@H](O)CC(OC(C)(C)CC1C=CC=CC=1)=O>>[Br:1][CH2:2][C@H:3]1[O:21][C:24]([CH3:25])([CH3:23])[O:20][C@@H:5]([CH2:6][C:7]([O:9][C:10]([CH3:18])([CH3:19])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:8])[CH2:4]1

Participants

3

Reactant 2

HCID 67607452(3R,5S)-2-methyl-1-phenylpropan-2-yl 6-chloro-3,5-dihydroxy-hexanoateHCID 67608343(3R,5S)-2-methyl-1-phenylpropan-2-yl 6-bromo-3,5-dihydroxy-hexanoate

Product 1

HCID 676061992-methyl-1-phenylpropan-2-yl 2-((4R,6S)-6-(bromomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Procedure

The procedure was carried out in the same manner as in Example 5, except that the crude compound (3R,5S)-2-methyl-1-phenylpropan-2-yl 6-bromo-3,5-dihydroxy-hexanoate (21.0 g) prepared in Example 4 was used in place of the crude compound (3R,5S)-2-methyl-1-phenylpropan-2-yl 6-chloro-3,5-dihydroxy-hexanoate (21.1 g) prepared in Example 3. The crude title compound was obtained (22.5 g).

Sources & evidence

ORD record
ord-44bccb47b2ad49ba81ede3851351a3dc
Source dataset
uspto-grants-2013_09
Patent number
US08524914B2

Reaction notes

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