Water → HCID 67313775, compound

HRID 1011998Notes

Reaction equation

HRID 1011998 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[C@@H:18]([CH3:19])[C@H:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:16][C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>C1COCC1>[CH2:7]([N:14]1[CH2:15][CH2:16][C@@H:17]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@@H:18]1[CH3:19])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67315641HCID 67315641, compound

Product 1

HCID 67313775HCID 67313775, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) suspension of lithium aluminium hydride (2.81 g, 74 mmol) in dry THF (30 ml) was added a solution of (4R,5S)-1-benzyl-4-benzyloxy-5-methyl-pyrrolidin-2-one (3.13 g, 11 mmol) (Tetrahedron 1998, 54, 12547) in THF (20 mL). The mixture was allowed to come to room temperature and stirred for 16 h after which lime it was cooled to 0° C. and water was cautiously added. The resulting suspension was the filtered over Hyflo, washing the salts with EtOAc. The filtrate was washed with brine, dried (Na2SO4) and concentrated. Purification by flash column chromatography (CH2Cl2:MeOH 98:2-5:95) afforded the title compound (1.5 g, 50%) as a yellow oil. MS: 282.2 (MH+).

Workup

  1. temperatureTo a cooled
  2. customto come to room temperature
  3. filtrationfiltered over Hyflo
  4. washwashing the salts with EtOAc
  5. washThe filtrate was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by flash column chromatography (CH2Cl2:MeOH 98:2-5:95)

Sources & evidence

ORD record
ord-457297847d7e49ae9ab40187d6129d06
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

Loading…