(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile → (S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[Z-2-(cyclohexyloxycarbonyl)-ethenyl]-cyclopropane-carboxylate

HRID 1995166Notes

Reaction equation

HRID 1995166 reaction equation
[CH3:1][C:2]1([CH3:19])[CH:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])[CH:3]1[C:16]([OH:18])=[O:17].[C:20]([C@@H:22](O)[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:24]=1)#[N:21]>>[CH3:1][C:2]1([CH3:19])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH:10]2[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]2)=[O:8])[C@H:3]1[C:16]([O:18][C@H:22]([C:20]#[N:21])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:24]=1)=[O:17]

Participants

3

Reactant 2

HCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 705231322,2-dimethyl-3-[Z-2-(cyclohexyloxycarbonyl)-ethenyl]-cyclopropane-carboxylic acid

Product 1

HCID 86739005(S)alpha-cyano-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[Z-2-(cyclohexyloxycarbonyl)-ethenyl]-cyclopropane-carboxylateYield 42.4%

Procedure

Using the procedure of Step D in Example 7, 2.5 g of the product of Step C and 2.2 g of (S)α-cyano-3-phenoxy-benzyl alcohol were reacted and the product was chromatographed over silica gel. Elution with a 9-1 hexane-ether mixture yielded 1.883 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(cyclohexyloxycarbonyl)-ethenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+41°±2.5° (c=0.5% in chloroform).

Workup

  1. customwere reacted
  2. customthe product was chromatographed over silica gel
  3. washElution with a 9-1 hexane-ether mixture

Sources & evidence

ORD record
ord-ca052f40de5e4b2597defe5560317ea4
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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