Sodium borohydride → (1S,3S)-6-chloro-3-phenylindan-1-ol

HRID 1047107Notes

Reaction equation

HRID 1047107 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:8]2=[O:11])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[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 4311764Sodium borohydrideHCID 11997855(S)-6-chloro-3-phenylindan-1-one

Product 1

HCID 11521607(1S,3S)-6-chloro-3-phenylindan-1-olYield 90.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-6-chloro-3-phenylindan-1-one (IVa) (isolated as in example 7) (23 g) is added in small portions to a suspension of sodium borohydride (1.6 g) in ethanol (160 ml) at 3-5° C. After the addition has been finalised, the mixture is allowed to reach room temperature. The reaction mixture is stirred for 2.75 hours, where after it is evaporated to dryness. The residue is dissolved in a mixture of water (150 ml) and ethyl acetate (200 ml), the phases are separated, and the water phase is extracted with ethyl acetate (100 ml). The organic phases are combined, washed with water (100 ml), dried with magnesium sulphate, filtered and evaporated to dryness. The residue is recrystallised from heptanes (250 ml), giving 20.9 g (90%) of the title product as a solid. Melting point 108.9° C., NMR conforms to structure, [α]D20 +48.30° (c=1.0, methanol). CHN calculated for C15H13OCl: C, 73.62; H, 5.35; found: C, 73.55; H, 5.29. >99% ee according to the chiral analysis.

Workup

  1. additionAfter the addition
  2. customto reach room temperature
  3. customwhere after it is evaporated to dryness
  4. dissolutionThe residue is dissolved in a mixture of water (150 ml) and ethyl acetate (200 ml)
  5. customthe phases are separated
  6. extractionthe water phase is extracted with ethyl acetate (100 ml)
  7. washwashed with water (100 ml)
  8. dry with materialdried with magnesium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness
  11. customThe residue is recrystallised from heptanes (250 ml)

Sources & evidence

ORD record
ord-c3c233d5d71745a2ab4bc0e484c2adfe
Source dataset
uspto-grants-2013_10
Patent number
US08569499B2

Reaction notes

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