rac-tert-butyl N-[(1r,4r)-4-formylcyclohexyl]carbamate → HCID 178489240, compound

HRID 1012933

Reaction equation

HRID 1012933 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[Li]CCCC.[C:17]([O:21][C:22](=[O:32])[NH:23][CH:24]1[CH2:29][CH2:28][CH:27]([CH:30]=[O:31])[CH2:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[C:17]([O:21][C:22](=[O:32])[NH:23][C@H:24]1[CH2:25][CH2:26][C@H:27]([CH:30]([OH:31])[C:10]2[S:11][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)[CH2:28][CH2:29]1)([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 11020615rac-tert-butyl N-[(1r,4r)-4-formylcyclohexyl]carbamateHCID 126318584-Methoxy-1,3-benzothiazoleHCID 178418339Butyllithium

Product 1

HCID 178489240HCID 178489240, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methoxy-benzothiazole (1.65 g, 10 mmol) in THF (50 ml) was added dropwise n-BuLi (2.5M in hexanes, 4 ml) so that the temperature did not exceed −70° C. The brown solution was stirred at this temperature for 15 min before dropwise addition of a solution of (4-formyl-cyclohexyl)-carbamic acid tert-butyl ester (1.14 g, 5 mmol) in THF (10 ml). The temperature was kept below −70° C. The brown solution was then gradually allowed to reach RT (over 3 h). The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOAc. The organic layer was washed with brine and dried over MgSO4 and concentrated under reduced pressure. The product was crystallised from ether to give 1.04 g (53%) of a white solid.

Workup

  1. customdid not exceed −70° C
  2. customwas kept below −70° C
  3. customto reach RT
  4. custom(over 3 h)
  5. customThe reaction mixture was quenched with saturated NH4Cl solution
  6. extractionextracted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customThe product was crystallised from ether

Sources & evidence

ORD record
ord-728534994fab4e25b1ea419fa9a3127e
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Linked notes

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