Tetrahydrofuran → (R)-2-(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1909721Notes

Reaction equation

HRID 1909721 reaction equation
C1COCC1.[C:6]([O:10][C:11]([N:13]1[CH2:17][CH2:16][CH2:15][C@@H:14]1[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([O:26]CC2C=CC=CC=2)=[CH:22][CH:21]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>CCO.[Pd]>[C:6]([O:10][C:11]([N:13]1[CH2:17][CH2:16][CH2:15][C@@H:14]1[CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)=[O:12])([CH3:9])([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68999348(R)-2-(4-Benzyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68999591(R)-2-(4-Hydroxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a 250 mL round bottomed flask which contained a suspension of Pd—C (10% wt, 3 g) in EtOH (70 mL) and THF (30 mL) was added (R)-2-(4-benzyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (3.5 g, 9 mmol). The stirred solution was flushed with a H2 balloon. This process was repeated 3 times. The resulting solution was stirred at rt under hydrogen atmosphere overnight. The reaction mixture was then filtered, washed with THF (30 ml), EtOH (25 ml) and dried in vacuo to provide the crude product which was further purified by recrystallization with ether-EtOAc-hexane to yield the title product, (2.5, 90%); MS; APCI+, Calcd: 293.5; Found m/z: 294.2 (M+1); 1H NMR (400 MHz, CDCl3); δ 1.47 (s, 9H), 1.80-2.10 (m, 4H), 3.40 (br, 2H), 3.69-3.89 (m, 1H), 4.00-4.18 (m 2H), 6.71-6.76 (m, 4H).

Workup

  1. customTo a 250 mL round bottomed flask which contained
  2. customThe stirred solution was flushed with a H2 balloon
  3. filtrationThe reaction mixture was then filtered
  4. washwashed with THF (30 ml), EtOH (25 ml)
  5. customdried in vacuo
  6. customto provide the crude product which
  7. customwas further purified by recrystallization with ether-EtOAc-hexane

Sources & evidence

ORD record
ord-098f5e944b4843099d9676cf10d08b09
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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