tert-Butyl (6-oxospiro[3.3]heptan-2-yl)carbamate → HCID 131733592, compound

HRID 1749517Notes

Reaction equation

HRID 1749517 reaction equation
[O:1]=[C:2]1[CH2:16][C:4]2([CH2:7][CH:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:5]2)[CH2:3]1.[CH3:17][Li]>C1COCC1>[OH:1][C:2]1([CH3:17])[CH2:3][C:4]2([CH2:7][CH:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:5]2)[CH2:16]1

Participants

4

Reactant 2

HCID 39872257tert-Butyl (6-oxospiro[3.3]heptan-2-yl)carbamateHCID 178418348HCID 178418348, compound

Product 1

HCID 131733592HCID 131733592, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (6-oxospiro[3.3]heptan-2-yl)carbamate (800 mg, 3.55 mmol) in anhydrous THF (15 mL) was added a solution of methyl lithium in THF (2.36 mL, 3 mol/L, 7.50 mmol) at −78° C. under nitrogen. The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with saturated aqueous ammonium chloride and the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated under vacuum to afford the title compound (760 mg, crude) as a brown solid, which was which was used to next step without further purification. MS (ESI) m/z 242.2 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4790baa0f3004be2bc890eb1508a521e
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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