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Bromomethylcyclopropane → ((S)-1-cyclopropylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester

HRID 1374552
Notes
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Reaction equation

HRID 1374552 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[C:14](=[O:15])[NH:13][C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:32][CH:33]1[CH2:35][CH2:34]1>O1CCCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][C@@H:8]1[C:14](=[O:15])[N:13]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81503BromomethylcyclopropaneHCID 2733832Lithium hexamethyldisilazaneHCID 22881971tert-butyl N-[(3S)-2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-3-yl]carbamate

Product 1

HCID 58595315((S)-1-cyclopropylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl esterYield 40%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-75 °C

Procedure

To a solution of 0.6 g (2.2 mmol) (S)-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester in 10 ml of tetrahydrofuran at −75° C. 2.2 ml (2.2 mmol) of lithium bis(trimethylsilyl)amide solution (1M in tetrahydrofurane) was added. After stirring for 30 min at −75° C. the mixture was allowed to reach room temperature and 0.35 g (2.6 mmol) of bromomethyl-cyclopropane was added. The mixture was stirred for 2.5 hours at room temperature and concentrated in vacuo. The residue was distributed between 1M NaHSO4 solution and ethyl acetate. The combined organic layers were re-extracted with water and dried (MgSO4) to yield 0.285 g (40%) of ((S)-1-cyclopropylmethyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)-carbamic acid tert-butyl ester.

Workup

  1. customat −75° C
  2. customto reach room temperature
  3. stirringThe mixture was stirred for 2.5 hours at room temperature
  4. concentrationconcentrated in vacuo
  5. extractionThe combined organic layers were re-extracted with water
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-71df74ed0e524c9788dac4ea43bb5d8d
Source dataset
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07166587B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes