Sodium Hydroxide → HCID 59598470, compound

HRID 2266274Notes

Reaction equation

HRID 2266274 reaction equation
[Cl:1][C:2]1[C:3]([F:29])=[C:4]([C@:8]([C@@H:16]2[O:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>CC#N.Cl>[Cl:1][C:2]1[C:3]([F:29])=[C:4]([C@:8]([C@@H:16]2[O:21][CH2:20][CH2:19][NH:18][CH2:17]2)([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 59598483HCID 59598483, compound

Product 1

HCID 59598470HCID 59598470, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (R)-tert-butyl 2-((R)-1-(3-chloro-2-fluorophenyl)-1-hydroxy-5-methoxypentyl)morpholine-4-carboxylate (0.38 g, 0.88 mmol) in MeCN (50 mL), 2 N aq HCl (50 mL) was added slowly at rt. The resulting solution was stirred at rt overnight, basified to pH=10 with 10 N aq NaOH, and evaporated under reduced pressure to remove MeCN. The aqueous layer was extracted with CH2Cl2 (4×5 mL). The combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed in vacuo to give (R)-1-(3-chloro-2-fluorophenyl)-5-methoxy-1-((R)-morpholin-2-yl)pentan-1-ol (0.27 g, 93%) as a free amine. The crude product was used for next step without purification; MS m/z 332 (M+H+).

Workup

  1. customevaporated under reduced pressure
  2. customto remove MeCN
  3. extractionThe aqueous layer was extracted with CH2Cl2 (4×5 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b8bb558560a347a19e5350c1999bb243
Source dataset
uspto-grants-2010_12
Patent number
US07858624B2

Reaction notes

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