Sodium borohydride → tert-Butyl ((2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-yl)carbamate

HRID 451821Notes

Reaction equation

HRID 451821 reaction equation
[CH2:1]([C@H:4]1[C:8](=[O:9])[N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:6]([C:17](OCC)=[O:18])[CH2:5]1)[CH:2]=[CH2:3].[BH4-].[Na+]>CO.O>[OH:18][CH2:17][C@@H:6]([NH:7][C:10](=[O:11])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:5][C@H:4]([CH2:8][OH:9])[CH2:1][CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 5287387(2S,4R)-1-tert-butyl 2-ethyl 4-allyl-5-oxopyrrolidine-1,2-dicarboxylate

Product 1

HCID 58011569tert-Butyl ((2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-yl)carbamateYield 85%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (2S,4R)-1-tert-butyl 2-ethyl 4-allyl-5-oxopyrrolidine-1,2-dicarboxylate (30 g, 0.1 mol) in MeOH/H2O (700/70 mL) was added NaBH4 (25 g, 0.66 mol), the resulting mixture was stirred 1 h at rt and quenched with sat. aq. NH4Cl (300 mL). The organic solvent was removed under vacuum and extracted with EA (3×250 mL). The combined organic phases were washed with brine (250 mL), dried over anhydrous Na2SO4, filtered and evaporated to afford the crude tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate (22 g, 85%). It was used for the next step without further purification. 1H NMR (CD3OD) δ 5.8-5.7 (m, 1H), 5.1-5.0 (m, 2H), 4.9-4.8 (d, 1H), 3.7-3.5 (m, 4H), 2.2-2.0 (m, 2H), 1.7-1.5 (m, 2H), 1.5-1.4 (s, 9H).

Workup

  1. customquenched with sat. aq. NH4Cl (300 mL)
  2. customThe organic solvent was removed under vacuum
  3. extractionextracted with EA (3×250 mL)
  4. washThe combined organic phases were washed with brine (250 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-438a6815fd664a16a4e240a9d0f46dab
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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