Sodium Sulfate → HCID 11219349, compound

HRID 2214966Notes

Reaction equation

HRID 2214966 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][C@H:3]1[F:15].[O-]S([O-])(=O)=O.[Na+].[Na+].[N:23]1[C:31]2[C:26](=[N:27][CH:28]=[C:29]([CH:32]=O)[CH:30]=2)[S:25][N:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCO>[F:15][C@@H:3]1[C@H:2]([NH:1][CH2:32][C:29]2[CH:30]=[C:31]3[N:23]=[N:24][S:25][C:26]3=[N:27][CH:28]=2)[CH2:7][CH2:6][NH:5][CH2:4]1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 112644351,1-Dimethylethyl (3R,4S)-4-amino-3-fluoro-1-piperidinecarboxylateHCID 11355675[1,2,3]Thiadiazolo[5,4-b]pyridine-6-carbaldehyde

Product 1

HCID 11219349HCID 11219349, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of cis-4-amino-1-tert-butoxycarbonyl-3-fluoropiperidine (1a) (1.00 mmole) in CH2Cl2 (5 mL) and EtOH (0.5 mL) is treated with anhydrous Na2SO4 (280 mg) and [1,2,3]thiadiazolo[5,4-b]pyridine-6-carboxaldehyde (1b) (1.10 mmole). The resulting solution is stirred at room temperature, then sodium triacetoxy borohydride (320 mg, 1.50 mmole) is added. The mixture is quenched by the addition of water (2 mL) and the volatiles removed in vacuo. Purification gives the desired compound.

Workup

  1. customThe mixture is quenched by the addition of water (2 mL)
  2. customthe volatiles removed in vacuo
  3. customPurification

Sources & evidence

ORD record
ord-88034d44eb614e7f9ae9cd02985f40b3
Source dataset
uspto-grants-2006_09
Patent number
US07109213B2

Reaction notes

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