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Cesium carbonate → (R)-tert-butyl (3-hydroxy-3-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)propyl)carbamate

HRID 2277042
Notes
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Reaction equation

HRID 2277042 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].CS([O:11][CH2:12][CH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)(=O)=O.[OH:19][C@@H:20]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33](O)[CH:32]=1)[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].[NH4+].[Cl-]>CN(C=O)C>[OH:19][C@@H:20]([C:31]1[CH:32]=[CH:33][CH:34]=[C:35]([O:11][CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:36]=1)[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 15166436Oxan-4-ylmethyl methanesulfonateHCID 90405310(R)-tert-butyl 3-hydroxy-3-(3-hydroxyphenyl)propylcarbamate

Product 1

HCID 90448349(R)-tert-butyl (3-hydroxy-3-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)propyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cs2CO3 (2.34 g, 7.18 mmol) was added to a solution of (tetrahydro-2H-pyran-4-yl)methyl methanesulfonate (1.05 g, 5.41 mmol) and Intermediate I (1.13 g, 4.23 mmol) in anhydrous DMF (11 mL) and the reaction mixture was heated at +70° C. under Ar for 22 hrs. Aqueous NH4Cl (25%) was added and the reaction mixture was extracted with MTBE twice. Combined organic layers were washed with brine, concentrated under reduced pressure. Purification by flash chromatography (25%-100% EtOAc-hexanes gradient) gave (R)-tert-butyl (3-hydroxy-3-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)propyl)carbamate as a colorless oil. Yield (0.47 g, 30%); 1H NMR (400 MHz, DMSO-d6) δ 7.18 (t, J=8.0 Hz, 1H), 6.85-6.84 (m, 2H), 6.76-6.74 (m, 2H), 5.15 (d, J=4.4 Hz, 1H), 4.49 (q, J=4.4 Hz, 1H), 3.88-3.84 (m, 2H), 3.79 (d, J=6.4 Hz, 2H), 2.94 (q, J=6.4 Hz, 2H), 1.70-1.62 (m, 4H), 1.38-1.26 (m, 11H).

Workup

  1. temperaturethe reaction mixture was heated at +70° C. under Ar for 22 hrs
  2. extractionthe reaction mixture was extracted with MTBE twice
  3. washCombined organic layers were washed with brine
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography (25%-100% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-5cd105993c4c4d4692882a051c192864
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09133154B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes