Acetic Acid → HCID 67257525, compound

HRID 1401849Notes

Reaction equation

HRID 1401849 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 258684-Amino-1-butanolHCID 1512679N-Boc-hexahydro-1H-azepin-4-oneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67257525HCID 67257525, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.09 g (4.65 mmol) of 4-oxoazepane-1-carboxylic acid tert-butyl ester and 864 μl (9.30 mmol) of 4-aminobutan-1-ol were suspended in 40 ml of ethanol, stirred at room temperature for 40 minutes, 532 μl (9.30 mmol) of glacial acetic acid were added, and the mixture was stirred for a further 10 min. Sodium triacetoxyborohydride (1.97 g, 9.30 mmol) was added, and the mixture was stirred at room temperature overnight and evaporated to dryness in vacuo. The residue was taken up in water and extracted 4 times with EA. The organic phase was dried over sodium sulfate, filtered and evaporated.

Workup

  1. stirringthe mixture was stirred for a further 10 min
  2. stirringthe mixture was stirred at room temperature overnight
  3. customevaporated to dryness in vacuo
  4. extractionextracted 4 times with EA
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c46cb561d03c444da9bb69517e2b0009
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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