Triethylsilane → HCID 13746617, compound

HRID 1433053Notes

Reaction equation

HRID 1433053 reaction equation
C(S[C:4](=[O:20])[C@H:5]([NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH:6]([CH3:8])[CH3:7])C.[SiH](CC)(CC)CC>CC(C)=O.[Pd]>[CH2:13]([O:12][C:10](=[O:11])[NH:9][C@@H:5]([CH:4]=[O:20])[CH:6]([CH3:8])[CH3:7])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 86592555HCID 86592555, compound

Product 1

HCID 13746617HCID 13746617, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution containing (R)-2-benzyloxycarbonylamino-3-methyl-thiobutyric acid S-ethyl ester (5.2 g, 17.6 mmol) in acetone (100 mL) is added Pd-on-C (10%, 233 mg). The heterogeneous mixture is cooled to 0° C. and Et3SiH (8.4 mL, 53 mmol) is quickly added. After 30 min, the reaction mixture is filtered through a pad of celite and the clear filtrate is concentrated to a residue which is partitioned between hexane (200 mL) and acetonitrile (300 mL). The layers are separated and the ACN phase is washed once with hexane (100 mL) and then concentrated to afford crude (R)-(1-Formyl-2-methyl-propyl)-carbamic acid benzyl ester (4.13 g) which is used directly without further purification. 1H NMR (300 MHz, CDCl3) δ2.30 (m, 1H), 4.31 (m, 1H), 5.09 (s, 2H), 5.45 (br, 1H), 7.30-7.45 (m, 5H), 9.65 (s, 1H) ppm.

Workup

  1. filtrationthe reaction mixture is filtered through a pad of celite
  2. concentrationthe clear filtrate is concentrated to a residue which
  3. customis partitioned between hexane (200 mL) and acetonitrile (300 mL)
  4. customThe layers are separated
  5. washthe ACN phase is washed once with hexane (100 mL)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a166f16751de4cfa97c44b93f1310c45
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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