Borane → 1,2,3,5,10,11a-Hexahydro-10-methyl-11H-pyrrolo[2,1-c] [1,4] benzodiazepin-11-one

HRID 268164

Reaction equation

HRID 268164 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=O)[N:5]2[CH2:14][CH2:15][CH2:16][CH:4]2[C:3]1=[O:17].CN1C(=O)OC(=O)C2=CC=CC=C12.N1CCC[C@@H]1C(O)=O.B>O1CCCC1.CO>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]2[CH2:14][CH2:15][CH2:16][CH:4]2[C:3]1=[O:17]

Participants

7

Reactant 4

HCID 6331BoraneHCID 8988D-ProlineHCID 25160N-Methylisatoic anhydrideHCID 985943610-methyl-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

Product 1

HCID 545015291,2,3,5,10,11a-Hexahydro-10-methyl-11H-pyrrolo[2,1-c] [1,4] benzodiazepin-11-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above compound is obtained when (-)-1,2,3,11 a-tetrahydro-10-methyl-5H-pyrrolo[2,1-c] [1,4] benzodiazepin- 5,11(10H)-dione, melting point 120-122°C. [α]D 25 - 477°, (1.24%, methanol) and (prepared from N-methylisatoic anhydride and D-proline as described in Example 1) is treated with borane in tetrahydrofuran as described in Example 1.

Workup

  1. customThe above compound is obtained

Sources & evidence

ORD record
ord-ad14593739a846938701f4f516ce75c5
Source dataset
uspto-grants-1976_03
Patent number
US03947408

Linked notes

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