Morpholine → HCID 69178046, compound

HRID 899629Notes

Reaction equation

HRID 899629 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][CH:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[C:1]([O:5][C:6](=[O:15])[NH2:7])([CH3:4])([CH3:3])[CH3:2].[N:16]1([CH:11]2[CH2:12][CH2:13][CH:8]([NH2:7])[CH2:9][CH2:10]2)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 69178046HCID 69178046, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-oxo-cyclohexyl)-carbamic acid tert-butyl ester (426 mg, 2.00 mmol) and morpholine (175 μL, 2.00 mmol) in CH2Cl2 (25 mL) and acetic acid (120 μL) was added sodium triacetoxyborohydride (636 mg, 3.00 mmol) and the mixture was stirred at room temperature overnight. The mixture was concentrated under reduced pressure and diluted with saturated aqueous sodium carbonate (30 mL). The aqueous layer was washed with CH2Cl2 (4×20 mL), and the combined organic extracts were dried (MgSO4), filtered, and concentrated under reduced pressure. Purification by flash column chromatography on silica gel (MeOH/CH2Cl2, 1:9) afforded the title compound as a white solid (76.2 mg, 13%). 1H NMR (CDCl3) δ 1.04-1.17 (m, 6H), 1.25-1.38 (m, 4H), 1.44 (s, 9H), 1.93 (d, 2H, J=12.0 Hz), 2.07 (d, 2H, J=12.0 Hz), 2.12-2.17 (m, 2H), 3.25-3.36 (br m, 1H), 4.35 (br m, 1H), 4.81 (br d, 1H).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additiondiluted with saturated aqueous sodium carbonate (30 mL)
  3. washThe aqueous layer was washed with CH2Cl2 (4×20 mL)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash column chromatography on silica gel (MeOH/CH2Cl2, 1:9)

Sources & evidence

ORD record
ord-0d96aa186fd74ba29aad6cac923ccf61
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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