Lithium triethylborohydride → HCID 59710338, compound

HRID 1864506Notes

Reaction equation

HRID 1864506 reaction equation
[Li+].[B-](CC)(CC)CC.[CH3:9][C:10]([Si:13]([CH3:34])([CH3:33])[O:14][C@H:15]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:16]1[CH2:27]OS(C)(=O)=O)([CH3:12])[CH3:11]>C1COCC1>[CH3:11][C:10]([Si:13]([CH3:34])([CH3:33])[O:14][C@H:15]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@@H:16]1[CH3:27])([CH3:9])[CH3:12]

Participants

4

Reactant 2

HCID 23712863Lithium triethylborohydrideHCID 59710219HCID 59710219, compound

Product 1

HCID 59710338HCID 59710338, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Superhydride (45.8 mL, 1M, 45.8 mmol) was added dropwise to an ice cold solution of 1,1-dimethylethyl(2R,3S)-3-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-2-{[(methylsulfonyl)oxy]methyl}-1-pyrrolidinecarboxylate (4.69 g, 11.47 mmol) in THF. The reaction was warmed to room temperature and stirred for 16 hours. The reaction was quenched with i-propanol until gas evolution ceased. The reaction was diluted with saturated NaHCO3 then extracted with ethyl acetate, dried over MgSO4 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography to yield the title compound (2.69 g, 8.5 mmol). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.0 (s, 6H), 0.8 (s, 9H), 1.0 (m, 3H), 1.4 (s, 9H), 1.6 (m, 1H), 2.0 (m, 1H), 3.3 (m, 2H), 3.5 (m, 1H), 4.0 (m, 1H). ES+=316.22.

Workup

  1. customThe reaction was quenched with i-propanol until gas evolution
  2. additionThe reaction was diluted with saturated NaHCO3
  3. extractionthen extracted with ethyl acetate
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d99326168f42450cb7838eb173a7e81d
Source dataset
uspto-grants-2009_12
Patent number
US07625909B2

Reaction notes

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