(Dimethyl sulfide)trihydroboron → (3S,5R)-3-Hydroxymethyl-5-methyl-nonanoic Acid Tert-butyl Ester

HRID 1795540Notes

Reaction equation

HRID 1795540 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][C@H:8]([CH2:12][C@H:13]([CH3:18])[CH2:14][CH2:15][CH2:16][CH3:17])[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2].CSC.B>C1COCC1>[C:1]([O:5][C:6](=[O:19])[CH2:7][C@@H:8]([CH2:9][OH:10])[CH2:12][C@H:13]([CH3:18])[CH2:14][CH2:15][CH2:16][CH3:17])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 54500721HCID 54500721, compound

Product 1

HCID 57065055(3S,5R)-3-Hydroxymethyl-5-methyl-nonanoic Acid Tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the crude acid 139 (6.14 mmol) in 30 mL THF at 0° C. was added borane-dimethyl sulfide complex (2.0 M solution in THF, 4.6 mL, 9.2 mmol), and the mixture was allowed to warm slowly to ambient temperature overnight. Additional BH3DMS was added until the acid was completely consumed (ca. 5 mL). The reaction was quenched by addition of MeOH, then partitioned between Et2O and sat. NaHCO3 (aq). The phases were separated, and the organic phase washed with brine, dried (MgSO4), and concentrated to provide alcohol 140. LRMS: m/z 226.1; 1H NMR (CDCl3): δ 3.63 (dd, J=11.0, 4.2 Hz, 1H), 3.42 (dd, J=11.0, 6.8 Hz, 1H), 2.30 (dd, J=14.9, 7.6 Hz, 1H), 2.20 (dd, J=14.9, 5.6 Hz, 1H), 2.03 (m, 2H), 1.42 (s, 9H), 1.24 (m, 6H), 1.02 (m, 2H), 0.85 (m, 6H). The crude product was used without purification.

Workup

  1. additionAdditional BH3DMS was added until the acid
  2. customwas completely consumed (ca. 5 mL)
  3. customThe reaction was quenched by addition of MeOH
  4. custompartitioned between Et2O and sat. NaHCO3 (aq)
  5. customThe phases were separated
  6. washthe organic phase washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f7ca649ea0a242bdb6ceac008ab96a72
Source dataset
uspto-grants-2006_04
Patent number
US07026505B2

Reaction notes

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