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

HRID 479054Notes

Reaction equation

HRID 479054 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 soln in THF, 4.6 mL, 9.2 mmol), and the mixture was allowed to warm slowly to ambient temperature overnight. Additional BH3-DMS 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): δ3.63 (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. customwas completely consumed (ca. 5 mL)
  2. customThe reaction was quenched by addition of MeOH
  3. custompartitioned between Et2O and sat. NaHCO3 (aq)
  4. customThe phases were separated
  5. washthe organic phase washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-64edf9b27f6743dda16b2c7aab5a50aa
Source dataset
uspto-grants-2003_11
Patent number
US06642398B2

Reaction notes

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