Vinyl butyrate → (1S,3S)-6-chloro-3-phenylindan-1-ol

HRID 500654Notes

Reaction equation

HRID 500654 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C@@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][C@H:8]2[OH:11])=[CH:4][CH:3]=1.C(OC(=O)CCC)=C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C@H:6]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:7][C@@H:8]2[OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31247Vinyl butyrateHCID 59245334Racemic cis-6-chloro-3-phenylindan-1-ol

Product 1

HCID 11521607(1S,3S)-6-chloro-3-phenylindan-1-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound V (5 g, 20.4 mmol) is dissolved in 150 ml anhydrous toluene. 0.5 g Novozym 435 (Candida Antarctica lipase B) (Novozymes A/S, Fluka Cat.-No. 73940) is added followed by vinylbutyrate (13 ml, 102.2 mmol). The mixture is stirred using mechanical stirrer at 21° C. After 1 day, an additional 0.5 g Novozym 435 is added. After 4 days at a conversion of 54%, the mixture is filtered and concentrated in vacuo to obtain an oil containing a mixture of (1R, 3R)-cis-6-chloro-3-phenylindan-1-ol-butyrate ester and desired compound Va with an enantiomeric excess of 99.2% (99.6% compound Va and 0.4% (1R, 3R)-cis-6-chloro-3-phenylindan-1-ol).

Workup

  1. addition73940) is added
  2. customat 21° C
  3. additionan additional 0.5 g Novozym 435 is added
  4. waitAfter 4 days at a conversion of 54%
  5. filtrationthe mixture is filtered
  6. concentrationconcentrated in vacuo
  7. customto obtain an oil
  8. additioncontaining

Sources & evidence

ORD record
ord-d9f7c4698bc54459948556d616a4abea
Source dataset
uspto-grants-2010_08
Patent number
US07772240B2

Reaction notes

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