Potassium Hydroxide → HCID 68706115, compound

HRID 1518245Notes

Reaction equation

HRID 1518245 reaction equation
[OH-].[K+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[N:18]([CH2:36][C@@:37]23[CH2:45][CH2:44][CH2:43][N:38]2C(=O)[O:40][CH2:41]3)[C:19]2[C:24]([C:25]=1[CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)=[CH:23][CH:22]=[C:21]([C:32]([O:34][CH3:35])=[O:33])[CH:20]=2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Si](C=[N+]=[N-])(C)(C)C>CO>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[N:18]([CH2:36][C@@:37]2([CH2:41][OH:40])[CH2:45][CH2:44][CH2:43][NH:38]2)[C:19]2[C:24]([C:25]=1[CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1)=[CH:23][CH:22]=[C:21]([C:32]([O:34][CH3:35])=[O:33])[CH:20]=2)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 167693TrimethylsilyldiazomethaneHCID 68708210HCID 68708210, compound

Product 1

HCID 68706115HCID 68706115, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1M aq. KOH (15 eq.) was added to a 0.08M solution of methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1-{[(7aR)-3-oxodihydro-1H-pyrrolo[1,2-c][1,3]oxazol-7a(5H)-yl]methyl}-1H-indole-6-carboxylate in MeOH, and the mixture was refluxed for 2 days. After quenching with an equivalent amount of aq. HCl and evaporation of volatiles, the residue was taken in toluene:MeOH 4:1 (0.1M) and treated at RT with excess (2.5 eq.) TMS-diazomethane for 1 h; evaporation of solvents gave crude methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1-{[(2R)-2-(hydroxymethyl)pyrrolidin-2-yl]methyl}-1H-indole-6-carboxylate. To a 0.1M solution of this material in dry DCM were added TEA (3 eq.) and Boc2O (1.5 eq.) and the mixture was stirred at RT overnight, after quenching with sat NaHCO3 the mixture was extracted with EtOAc, washed with brine, dried and concentrated; chromatography (PE/EtOAc 2:1) afforded the title compound (57%).

Workup

  1. temperaturethe mixture was refluxed for 2 days
  2. customAfter quenching with an equivalent amount of aq. HCl and evaporation of volatiles
  3. customevaporation of solvents

Sources & evidence

ORD record
ord-3c42d43616c94a489390800ea992ee9a
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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