Sodium Chloride → HCID 52951550, compound

HRID 1517555Notes

Reaction equation

HRID 1517555 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:11]3[S:12][CH:13]=[CH:14][C:10]=3[CH2:9][CH2:8][O:7]2)[CH2:3][CH2:2]1.C(=O)(OC(C)(C)C)[O:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O.[Cl-].[Na+]>CC1CCCO1>[N:1]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:16])[CH2:2][CH2:3][C:4]2([C:11]3[S:12][CH:13]=[CH:14][C:10]=3[CH2:9][CH2:8][O:7]2)[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 90495Di-tert-butyl dicarbonateHCID 529515494',5'-Dihydrospiro[piperidine-4,7'-thieno[2,3-c]pyran]

Product 1

HCID 52951550HCID 52951550, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent2×

Procedure

Spiro[4,5-dihydrothieno[2,3-c]pyran-7,4′-piperidine] (60 g, 286.6 mmol) in 2-methyltetrahydrofuran (600 mL) is stirred at 22° C. for 10 min. Then, tert-butoxycarbonyl tert-butyl carbonate (65.6 g, 301 mmol) in 2-methyltetrahydrofuran (300 mL) is added dropwise. After 12 hr., an aqueous solution of sodium chloride (250 mL) is added and the organic layer is separated. The aqueous layer is washed twice with 2-methyltetrahydrofuran (2×50 mL) and the organic layers are combined and washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound in 99% yield. MS (m/z): 310 (M+1).

Workup

  1. customthe organic layer is separated
  2. washThe aqueous layer is washed twice with 2-methyltetrahydrofuran (2×50 mL)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f0d1ad3810fd4df2b54878c61c2ba30c
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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