Hydrochloric Acid → tert-Butyl 4-hydroxyazepane-1-carboxylate

HRID 1689772Notes

Reaction equation

HRID 1689772 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].Cl>CO.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1512679N-Boc-hexahydro-1H-azepin-4-oneHCID 4148881Lithium borohydride

Product 1

HCID 22933363tert-Butyl 4-hydroxyazepane-1-carboxylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-oxo-azepane-1-carboxylic acid tert-butyl ester (13.6 g, 63.8 mmol) in methanol (10 mL) and tetrahydrofuran (30 mL) at 0° C. is added lithium borohydride (1.40 g, 63.8 mmol). The mixture is stirred at 0° C. for 60 minutes. Hydrochloric acid (1.0 M, 40 mL) is added. The mixture is concentrated under reduced pressure and extracted with ethyl acetate (2×). The combined ethyl acetate layers are dried (Na2SO4) and concentrated to a residue. The residue is purified on silica using a gradient of ethyl acetate in hexanes (40 to 80%) to yield the title compound (13.6 g, 99.1%).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. extractionextracted with ethyl acetate (2×)
  3. dry with materialThe combined ethyl acetate layers are dried (Na2SO4)
  4. concentrationconcentrated to a residue
  5. customThe residue is purified on silica using a gradient of ethyl acetate in hexanes (40 to 80%)

Sources & evidence

ORD record
ord-a90266e1b8d5460bb5f257d630056c46
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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