Methyl iodide → [(3R)-hexahydro-1-methyl-2-oxo-1H-azepin-3-yl]-carbamic acid, 1,1-dimethylethyl ester

HRID 1353436Notes

Reaction equation

HRID 1353436 reaction equation
[O:1]=[C:2]1[C@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][CH2:6][CH2:5][CH2:4][NH:3]1.[CH3:17]I>C1COCC1>[CH3:17][N:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:2]1=[O:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 2756761(R)-tert-Butyl (2-oxoazepan-3-yl)carbamate

Product 1

HCID 21101878[(3R)-hexahydro-1-methyl-2-oxo-1H-azepin-3-yl]-carbamic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of [(3R)-hexahydro-2-oxo-1H-azepin-3-yl]-carbamic acid, 1,1-dimethylethyl ester (500 mg) in THF (5 mL) at rt, KHDMS (5.26 mL, 1.0 M in THF) was added. After 30 min, CH3I (0.26 mL) was introduced. The reaction was kept at rt overnight, and then quenched with brine. The reaction mixture was extracted with EtOAc, washed with brine, and dried over Na2SO4. Concentration in vacuo afforded the crude product which was used directly for the next step reaction without further purification.

Workup

  1. waitThe reaction was kept at rt overnight
  2. customquenched with brine
  3. extractionThe reaction mixture was extracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-72db042ac0104512ab8638e01f323291
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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