Lithium borohydride → Benzyl (3S,4R)-1-(tert-butoxycarbonyl)-4-formylpyrrolidin-3-ylcarbamate

HRID 456259Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13](OCC)=[O:14])[C@H:10]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-]>C1COCC1.O=[Mn]=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH:13]=[O:14])[C@H:10]([NH:18][C:19](=[O:28])[O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of benzyl (3S*,4R*)-1-(tert-butoxycarbonyl)-4-(ethoxycarbonyl)pyrrolidin-3-ylcarbamate (4.4 g, 11.2 mmol) in 150 mL THF, LiBH4 (0.74 g, 33.6 mmol) was added and the mixture was stirred at 80° C. for 1.5 hours. The mixture was quenched with H2O, extracted with EtOAc, the combined organic extracts were dried with Na2SO4 and evaporated. The residue was re-dissolved in 300 mL CH2Cl2, activated MnO2 (3.86 g, 56 mmol) was added and the mixture was stirred for 24 hours at room temperature. MnO2 was filtered off through Celite, and the filtrate was evaporated giving the title aldehyde.

Workup

customThe mixture was quenched with H2O
extractionextracted with EtOAc
dry with materialthe combined organic extracts were dried with Na2SO4
customevaporated
dissolutionThe residue was re-dissolved in 300 mL CH2Cl2
stirringthe mixture was stirred for 24 hours at room temperature
filtrationMnO2 was filtered off through Celite
customthe filtrate was evaporated

Sources & evidence

ORD record: ord-0577f149cd0344748dc03bd68d7b010d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497383B2

Reaction notes

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