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

HRID 1995181Notes

Reaction equation

HRID 1995181 reaction equation
[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[C@H:3]1[C:13](OC(C)(C)C)=[O:14].[C:21]([C@@H:23]([OH:37])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:25]=1)#[N:22]>>[CH3:1][C:2]1([CH3:20])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH2:10][C:11]#[CH:12])=[O:8])[C@H:3]1[C:13]([O:37][C@H:23]([C:21]#[N:22])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:25]=1)=[O:14]

Participants

3

Reactant 2

HCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 86739014tert.-butyl(1R,cis)2,2-dimethyl-3-[Z-2-(propargyloxy-carbonyl)-ethenyl]cyclopropane-carboxylate

Product 1

HCID 86739016(S)alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(propargyloxycarbonyl)-ethenyl]-cyclopropane-carboxylateYield 116.6%

Procedure

Using the procedure of Step C of Example 13, 1.59 g of the product of Step A and 1.8 g of (S)α-cyano-3-phenoxy-benzyl alcohol were reacted and after 2 hours, the mixture was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 9-1 cyclohexane-ethyl acetate mixture yielded 2.86 g of (S)α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(propargyloxycarbonyl)-ethenyl]-cyclopropane-carboxylate with a specific rotation of [α]D20 =+44°±1.5° (c=1% in CHCl3).

Workup

  1. customwere reacted and after 2 hours
  2. filtrationthe mixture was filtered
  3. customThe filtrate was evaporated to dryness under reduced pressure
  4. customthe residue was chromatographed over silica gel
  5. washElution with a 9-1 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-69b58d7db146423fa682cca86c11f7d4
Source dataset
uspto-grants-1983_09
Patent number
US04402972

Reaction notes

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