benzyl 2,4-bis(benzyloxy)-6-(2-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-5-methylnicotinate → benzyl 6-(2-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-2,4-bis(benzyloxy)-5-methylnicotinate

HRID 1481793Notes

Reaction equation

HRID 1481793 reaction equation
[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH:35]([NH:37]C(OC(C)(C)C)=O)[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[C:22]([CH3:45])=[C:21]([O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[NH2:37][CH:35]1[CH2:34][N:30]2[C:31]3[CH:32]=[CH:33][C:25]([C:23]4[C:22]([CH3:45])=[C:21]([O:46][CH2:47][C:48]5[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=5)[C:10]([C:11]([O:13][CH2:14][C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=5)=[O:12])=[C:9]([O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[N:24]=4)=[CH:26][C:27]=3[CH:28]=[C:29]2[CH2:36]1

Participants

3

Reactant 1

HCID 71284342benzyl 2,4-bis(benzyloxy)-6-(2-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-5-methylnicotinate

Product 1

HCID 71284437benzyl 6-(2-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-2,4-bis(benzyloxy)-5-methylnicotinateYield 65.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The intermediate from Step 3 (65 mg, 0.09 mmol) was dissolved in trifluoroacetic acid (1 mL). After 1 min of stirring at room temperature, the mixture was partitioned in CH2Cl2 and aqueous 1 M K2CO3. The organic layer was removed, concentrated and chromatographed on silica gel (0-8% MeOH in CH2Cl2) to provide the product as a white powder (36 mg, 64%).

Workup

  1. customthe mixture was partitioned in CH2Cl2
  2. customThe organic layer was removed
  3. concentrationconcentrated
  4. customchromatographed on silica gel (0-8% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1b58216a6a804c4d811369cd57b244bc
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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