Sodium borohydride → HCID 66627373, compound

HRID 1664963Notes

Reaction equation

C(OC([C@@H]1C[C@H]1CNC(OC(C)(C)C)=O)=O)C.[CH3:18][O:19][C:20]([C@@H:22]1[CH2:25][CH2:24][C@H:23]1[CH:26]([NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])S(C1C=CC(C)=CC=1)(=O)=O)=[O:21].[BH4-].[Na+]>>[CH3:18][O:19][C:20]([C@@H:22]1[CH2:25][CH2:24][C@H:23]1[CH2:26][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:21]

Participants

Reactant 3

HCID 4311764Sodium borohydride

HCID 57918176HCID 57918176, compound2×

HCID 66627829HCID 66627829, compound

Product 1

HCID 66627373HCID 66627373, compoundYield 73.4%

Procedure

According to the synthesis of Trans-2-(tert-Butoxycarbonylamino-methyl)-cyclopropanecarboxylic acid ethyl ester (intermediate L, example 43), the title compound was prepared from Trans-2-[tert-Butoxycarbonylamino-(toluene-4-sulfonyl)-methyl]-cyclobutanecarboxylic acid methyl ester (17.7 g, 44.53 mmol), sodium borohydride (3.3 g, 83.74 mmol) and 8.2 g, (33.7 mmol, 73.4% yield) was obtained. MS (m/e): 244.0 (M+H+).

Workup

custom(33.7 mmol, 73.4% yield) was obtained

Sources & evidence

ORD record: ord-b3bc734af3bb4303b1b50f573e4eaa67
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039490B2

Reaction notes

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