Tetrahydrofuran → (S)-6-Amino-2-carbazol-9-yl-hexanoic methyl ester

HRID 449756

Reaction equation

HRID 449756 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([N:21]1[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:17]([O:19][CH3:20])=[O:18])=O)C1C=CC=CC=1.C1COCC1>[Pd].C(O)(C)C>[CH3:20][O:19][C:17](=[O:18])[C@@H:16]([N:21]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[C:28]2[C:33]1=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:15][CH2:14][CH2:13][CH2:12][NH2:11]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67993166(S)-methyl 6-benzyloxycarbonylamino-2-carbazol-9-yl-hexanoate

Product 1

HCID 67993118(S)-6-Amino-2-carbazol-9-yl-hexanoic methyl esterYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

10% Pd/C (0.100 g) was added in one portion to a stiffed solution of (S)-Methyl 6-benzyloxycarbonylamino-2-carbazol-9-yl-hexanoate 3 (1.06 g, 2.47 mmol) in a (1:1) mixture of THF (10 mL) and isopropanol (10 mL) under nitrogen atmosphere. The reaction mixture was subsequently stirred under hydrogen atmosphere for 4 h at room temperature. The reaction mixture was filtrated through a celite pad and the filtrate was evaporated under reduced pressure to get (S)-6-amino-2-carbazol-9-yl-hexanoic methyl ester 4 (0.640 g, 85%) as off-white solid.

Workup

  1. filtrationThe reaction mixture was filtrated through a celite pad
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-28d0170c07274af5b5670d2aa0f7528e
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Linked notes

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