Hydrochloric Acid → (2R,4R)-[4-(4-Bromo-2-nitro-phenylamino)-pyrrolidin-2-yl]-methanol, hydrochloride

HRID 244352Notes

Reaction equation

HRID 244352 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:15]=2[N+:21]([O-:23])=[O:22])[CH2:10][C@@H:9]1[CH2:24][OH:25])=O)(C)(C)C.[ClH:26]>ClCCl.O1CCOCC1>[ClH:26].[Br:20][C:17]1[CH:18]=[CH:19][C:14]([NH:13][C@H:11]2[CH2:12][NH:8][C@@H:9]([CH2:24][OH:25])[CH2:10]2)=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58564432(2R,4R)-4-(4-Bromo-2-nitro-phenylamino)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 131731204(2R,4R)-[4-(4-Bromo-2-nitro-phenylamino)-pyrrolidin-2-yl]-methanol, hydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (2R,4R)-4-(4-bromo-2-nitro-phenylamino)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (125.5 g, 0.301 mol) in dichloromethane (400 mL) add 4 N hydrochloric acid in dioxane (800 mL) and stir for 4 h at room temperature. Collect the precipitate by filtration, wash with ether and dry at 20 mm Hg/60° C. to obtain the title compound (105.2 g, 99%). [α]D20−89.6 (c=1.0 in methanol). 1H NMR (400 MHz, DMSO-d6) δ 1.80-1.85 (m, 1H), 2.54-2.59 (m, 1H), 3.43-3.51 (m, 3H), 3.56-3.63 (m, 1H), 3.69-3.72 (m, 2 H), 4.50-4.51 (m, 1H), 5.60 (br s, 1H), 7.10 (d, 1H), 7.65 (dd, 1H), 8.14 (d, 1H), 8.95 (br s, 1H), 9.91 (br s, 1H).

Workup

  1. customCollect the precipitate
  2. filtrationby filtration
  3. washwash with ether
  4. customdry at 20 mm Hg/60° C.

Sources & evidence

ORD record
ord-55140907a86244858685ecb73de1da8b
Source dataset
uspto-grants-2014_02
Patent number
US08658638B2

Reaction notes

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