Methanol → HCID 86726330, compound

HRID 629730Notes

Reaction equation

HRID 629730 reaction equation
[Si:1]([O:18][CH2:19][C@H:20]1[N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][C@@H:23]([CH:33]([F:44])[CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[N+:41]([O-])=O)[O:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.CO.O>C(Cl)Cl.[Fe]>[NH2:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[CH2:34][CH:33]([C@H:23]1[O:22][CH2:21][C@@H:20]([CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24]1)[F:44]

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8028TetrahydrofuranHCID 86726331HCID 86726331, compound

Product 1

HCID 86726330HCID 86726330, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of intermediate tert-butyl (2S,5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-[1-fluoro-2-(2-nitrophenyl)ethyl]morpholine-4-carboxylate (1 eq.) in a mixture 5:2:1 THF:MeOH:H2O (0.002 M) was warmed up to +59° C. and treated with solid iron (223 eq.). The mixture was further stirred at the same temperature for 45 min, diluted with DCM, washed with sat. NaHCO3, dried over MgSO4, filtered and concentrated. The product was submitted to the next step without further purification. Light yellow oil.

Workup

  1. washwashed with sat. NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe product was submitted to the next step without further purification

Sources & evidence

ORD record
ord-f4ef82177cf9443ea45f5126df6617e2
Source dataset
uspto-grants-2016_04
Patent number
US09315475B2

Reaction notes

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