Aluminium lithium hydride → Tert-butyl 3-formylcyclohexyl(methyl)carbamate

HRID 2115665Notes

Reaction equation

HRID 2115665 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].CON(C)[C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13]1)=[O:11]>CCOCC>[CH:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH:14]([N:18]([CH3:26])[C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22258869tert-butyl N-[3-(N-methoxy-N-methylcarbamoyl)cyclohexyl]-N-methylcarbamate

Product 1

HCID 23590653Tert-butyl 3-formylcyclohexyl(methyl)carbamateYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) suspension of LiAlH4 (380 mg, 9.9 mmol) in Et2O (40 mL) was added dropwise a solution of tert-butyl N-[3-(N-methoxy-N-methylcarbamoyl)cyclohexyl]-N-methylcarbamate (2.38 g, 7.92 mmol) in Et2O (40 mL) over 10 min. The reaction mixture was stirred at 0° C. for 0.5 hr, and quenched with 1N KHSO4 (100 mL). The organic phase was separated, dried over MgSO4 and evaporated to give tert-butyl 3-formylcyclohexyl(methyl)carbamate as a colorless oil, which was used for next step without purification (1.66 g, yield; 87%).

Workup

  1. customquenched with 1N KHSO4 (100 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-7d8eaa13630b4b9bb3e3d068610b21b8
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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