Tert-Butylamine → Tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamide

HRID 742871Notes

Reaction equation

HRID 742871 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH:12]1[C:24](O)=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:29]1CCOCC1)C.ClC(O[CH2:39][CH:40]([CH3:42])[CH3:41])=O.C(N)(C)(C)C>O1CCCC1.C(OCC)(=O)C>[C:40]([C:12]1([C:24]([NH2:29])=[O:25])[C:13]2[NH:14][C:15]3[C:20]([C:21]=2[CH2:22][CH2:23][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])=[CH:19][CH:18]=[CH:17][CH:16]=3)([CH3:42])([CH3:41])[CH3:39]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 7525EthylmorpholineHCID 62365Isobutyl chloroformateHCID 190319922-[(benzyloxy)carbonyl]-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1-carboxylic acid

Product 1

HCID 86746252Tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4.54 g of 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxylic acid in 45 ml of anhydrous tetrahydrofuran was cooled, while protecting with a drying tube, in an ice/acetone bath. 1.82 ml of N-ethylmorpholine and 1.82 ml of isobutyl chloroformate were added, the mixture was stirred for 10 minutes and then 2.1 ml of tert.butylamine were added. The mixture was then stirred at 0° C. for 40 minutes and at room temperature for 45 minutes, diluted with ethyl acetate and washed twice with water, twice with 0.5M sodium hydroxide solution and again with water. The solution was dried over magnesium sulphate and evaporated to dryness. Recrystallization from ethyl acetate and n-hexane gave 1.21 g of tert.butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-1-carboxamide; MS: m/e 406 [M+H]+. A further 0.76 g of identical material was obtained by subjecting the mother liquors to chromatography on silica gel using ethyl acetate/n-hexane (1:1) for the elution.

Workup

  1. customwhile protecting with a drying tube, in an ice/acetone bath
  2. stirringThe mixture was then stirred at 0° C. for 40 minutes and at room temperature for 45 minutes
  3. washwashed twice with water, twice with 0.5M sodium hydroxide solution and again with water
  4. dry with materialThe solution was dried over magnesium sulphate
  5. customevaporated to dryness
  6. customRecrystallization from ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-262c8a126da6476c86ba9810c97731e6
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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