tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate → HCID 67315283, compound

HRID 1012941Notes

Reaction equation

HRID 1012941 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]([N:24]1[CH2:29][CH2:28][CH:27]([C:30](=[O:35])N(OC)C)[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C1COCC1>[C:17]([O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([C:30]([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)=[O:35])[CH2:26][CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylateHCID 126318584-Methoxy-1,3-benzothiazoleHCID 178418339Butyllithium

Product 1

HCID 67315283HCID 67315283, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methoxybenzothiazole (413 mg, 2.5 mmol) in THF (10 ml) at −75° C. was added dropwise n-BuLi (2.5M in Hex, 1.1 ml) such that the temperature did not exceed −70° C. The brown solution was stirred at this temperature for 15 min before the dropwise addition of a solution of 4-(methoxy-methyl-carbamoyl)-piperidine-1-carboxylic acid tert-butyl ester (680 mg, 2.5 mmol) in THF (2 ml). The temperature was also kept below −70° C. The brown solution was then gradually allowed to reach RT (over 3 h). The mixture was poured on water and extracted with EtOAc. Organic extracts were washed with brine and dried over MgSO4 and concentrated. Chromatography on SiO2 (hex/EtOAc 2:1) gave 565 mg (60%) of a yellowish solid.

Workup

  1. customdid not exceed −70° C
  2. customwas also kept below −70° C
  3. customto reach RT
  4. custom(over 3 h)
  5. additionThe mixture was poured on water
  6. extractionextracted with EtOAc
  7. washOrganic extracts were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f7c83247326a447bba017d5b5c287eeb
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Reaction notes

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