Borane → HCID 44303835, compound

HRID 486763Notes

Reaction equation

HRID 486763 reaction equation
[CH2:1]([N:6]([CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:29])[N:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:11]([C:30](O)=[O:31])[CH2:10]1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].B>C1COCC1>[CH2:33]([N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:29])[N:16]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:11]([CH2:30][OH:31])[CH2:10]1)=[O:8])[CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 6331BoraneHCID 22850669HCID 22850669, compound

Product 1

HCID 44303835HCID 44303835, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.24 g (2.44 mmole) of (S)-4-(dipentylcarbamoyl)-1-(diphenylcarbamoyl)piperazine-2-carboxylic acid dissolved in 6 ml of THF was cooled to 0° in an ice bath. To this 9 ml (9 mmole) of 1.0M borane solution in THF was slowly added during a 15 min. period. The resulting mixture was stirred for 24 hr at 25°. The excess hydride was destroyed carefully with 20 ml of a 1:1 mixture of THF and water. The aqueous phase was saturated with anhydrous potassium carbonate. The THF layer was separated and aqueous layer was extracted with ether. The combined organic phase was dried over magnesium sulfate. The solvents were removed on a rotary evaporator to yield 1.18 g (98%) of (S)-4-(dipentylcarbamoyl)-1-(diphenyl-carbamoyl)-2-(hydroxymethyl)piperazine as a white solid, mp 133°-134°.

Workup

  1. temperaturewas cooled to 0° in an ice bath
  2. customThe excess hydride was destroyed carefully with 20 ml of a 1:1 mixture of THF and water
  3. customThe THF layer was separated
  4. extractionaqueous layer was extracted with ether
  5. dry with materialThe combined organic phase was dried over magnesium sulfate
  6. customThe solvents were removed on a rotary evaporator

Sources & evidence

ORD record
ord-7eb8349ad6234835bc291e002399d6a2
Source dataset
uspto-grants-1994_03
Patent number
US05292726

Reaction notes

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