Hydrochloric Acid → (R)-benzyl 2-(4-(hydroxymethyl)oxazol-2-yl)pyrrolidine-1-carboxylate

HRID 2071111Notes

Reaction equation

HRID 2071111 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]1[O:17][CH:18]=[C:19]([C:21](OC)=[O:22])[N:20]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[BH4-].C(OCC)(=O)C.Cl>C1COCC1.O>[OH:22][CH2:21][C:19]1[N:20]=[C:16]([C@H:12]2[CH2:13][CH2:14][CH2:15][N:11]2[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[O:17][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 66697570(R)-methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)oxazole-4-carboxylate

Product 1

HCID 86647435(R)-benzyl 2-(4-(hydroxymethyl)oxazol-2-yl)pyrrolidine-1-carboxylateYield 64.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-methyl 2-(1-(benzyloxycarbonyl)pyrrolidin-2-yl)oxazole-4-carboxylate (6.95 g, 21.1 mmoles) in THF (50 mL) at 0° C., was added LiBH4 (32 mL, 2.0M in THF, 63.2 mmoles). The reaction was allowed to warm to room temperature and stirred for 3 h. Ethyl acetate (25 mL) was added drop-wise and stirred for 30 min. The reaction was cooled to 0° C. and 50 mL of 1N HCl was added drop-wise and diluted with 100 mL of water. It was then extracted with ethyl acetate, dried on Na2SO4, concentrated, and chromatographed on silica gel (3% MeOH/97% chloroform) to yield 4.1 g of (R)-benzyl 2-(4-(hydroxymethyl)oxazol-2-yl)pyrrolidine-1-carboxylate.

Workup

  1. stirringstirred for 30 min
  2. temperatureThe reaction was cooled to 0° C.
  3. extractionIt was then extracted with ethyl acetate
  4. customdried on Na2SO4
  5. concentrationconcentrated
  6. customchromatographed on silica gel (3% MeOH/97% chloroform)

Sources & evidence

ORD record
ord-b4f11826b647456bb61f325cc32d760b
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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