Sodium borohydride → HCID 20376337, compound

HRID 2052715Notes

Reaction equation

HRID 2052715 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:8]=2[N:9]([CH2:17][CH2:18]3)[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1.C(O)C.C1COCC1.[BH4-].[Na+]>O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]2[CH2:17][CH2:18][C:19]3=[CH:20][CH:21]=[CH:22][C:7]1=[C:8]23

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 20376324HCID 20376324, compoundHCID 21873804Tetrahydrofuran ethanol

Product 1

HCID 20376337HCID 20376337, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

An ice cold solution of 8.88 g of 1,2-dihydro-6-furylindolo[1,7-ab][1,5]benzodiazepine (HCl salt) in 100 ml 3:1 absolute ethanol-THF is treated portionwise with 2.5 g NaBH4 added at such a rate as to minimize foaming. After stirring for 1.5 hours at 0° C., water is added dropwise and the product is partitioned in CH2Cl2 -water. The aqueous phase is extracted with CH2Cl2 and the combined organic portions are washed with brine, dried over K2CO3, and concentrated to an oil which solidifies upon standing to yield 6-furyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine, m.p. 141°-144° C.

Workup

  1. additionadded at such a rate as
  2. customthe product is partitioned in CH2Cl2 -water
  3. extractionThe aqueous phase is extracted with CH2Cl2
  4. washthe combined organic portions are washed with brine
  5. dry with materialdried over K2CO3
  6. concentrationconcentrated to an oil which

Sources & evidence

ORD record
ord-d01f069bd4be40f38b5141fa6a88b806
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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