Sodium triacetoxyborohydride → (R)-tert-butyl 2-((6-(methoxycarbonyl)-2,3-dihydro-1H-inden-1-ylamino)methyl)-1H-pyrrole-1-carboxylate

HRID 1253662Notes

Reaction equation

HRID 1253662 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH2:9][C@H:8]2[NH2:14])=[O:4].[CH:15]([C:17]1[N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:19](C)=[CH:20][CH:21]=1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11]([CH2:10][CH2:9][C@H:8]2[NH:14][CH2:15][C:17]2[N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:19]=[CH:20][CH:21]=2)=[CH:12][CH:13]=1)=[O:4]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 55278060(R)-Methyl 3-amino-2,3-dihydro-1H-indene-5-carboxylateHCID 59473746tert-Butyl 2-formyl-5-methyl-1H-pyrrole-1-carboxylate

Product 1

HCID 59505448(R)-tert-butyl 2-((6-(methoxycarbonyl)-2,3-dihydro-1H-inden-1-ylamino)methyl)-1H-pyrrole-1-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
25 °C

Procedure

A solution of (3R)-3-amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester (A-03) (361 mg, 1.88 mmol, 1 eq.) in methylene chloride (3 ml) was added to a solution of tert-butyl 2-formyl-5-methyl-1H-pyrrole-1-carboxylate (434 mg, 2.08 mmol, 1.1 eq.) in dry methylene chloride (17 ml) at 0° C. and the resulting reaction mixture was stirred at 25° C. for 2 h. The reaction mixture was cooled to 0° C. and then Na(OAc)3BH (1.2 g, 5.66 mmol, 3 eq.) was added portionwise and it was stirred at 25° C. for 14 h. The reaction mixture was diluted with methylene chloride (200 ml) and washed with saturated sodium bicarbonate (50 ml), water (2×50 ml) and brine (50 ml), and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (silica gel; 5% EtOAc/hexanes) to give the desired product as a light yellow oil. Yield: 82% (600 mg, 1.56 mmol).

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. stirringit was stirred at 25° C. for 14 h
  4. washwashed with saturated sodium bicarbonate (50 ml), water (2×50 ml) and brine (50 ml)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel; 5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c9f2ade0ac394b48a891694669514fd2
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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